Boron triene annulation. Substrate structural effects on steroidal annulation

TD Fulmer, TA Bryson

Index: Fulmer, T. D.; Bryson, T. A. Journal of Organic Chemistry, 1989 , vol. 54, p. 3496 - 3500

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Citation Number: 7

Abstract

In principle boron annulation of trienes (eg 1) is well-suited for the synthesis of steroids1 and other carbocycles. 2 To illustrate, carborane 2 could be formed by successive inter-and intramolecular borane-olefin additions with 1 (eq 1). Carbonylation of boracyclane 2 followed by oxidation would provide the steroid nucleus (3) in which the stereochemistry is derived from the defined chiral center in substrate 1. In practice, attempted boron ...